Downtown Winter Garden Vacation Packages for 2025

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Downtown Winter Garden Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
Aug 24 - Aug 28
found 21 hours ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Aug 24 - Aug 28
found 21 hours ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Aquatica and Universal’s Volcano Bay are located nearby.

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 28
found 21 hours ago
Roundtrip flight included
New York (LGA) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

The Smart Stay Inn

The Smart Stay Inn

2.5 out of 5
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Book a stay at this business-friendly motel in St. Augustine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Castillo de San Marcos National Monument and St. George Street are located nearby.

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Top Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
15.93 km from Downtown Winter Garden
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
22.81 km from Downtown Winter Garden
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr, Orlando, FL
23.33 km from Downtown Winter Garden
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
25.66 km from Downtown Winter Garden
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
18.41 km from Downtown Winter Garden
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in ...
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
23.65 km from Downtown Winter Garden
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
15.64 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 out of 5
14500 Continental Gateway, Orlando, FL
24.34 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd, Orlando, FL
18.68 km from Downtown Winter Garden
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr, Orlando, FL
22.48 km from Downtown Winter Garden
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
20.63 km from Downtown Winter Garden
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

3 out of 5
2000 Hotel Plaza Boulevard, Lake Buena Vista, FL
22.13 km from Downtown Winter Garden
Stay at this 3-star business-friendly hotel in Lake Buena Vista. Enjoy free breakfast, free WiFi, and 3 restaurants. Our guests praise the breakfast and the ...
Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

3 out of 5
7125 Universal Boulevard, Orlando, FL
16.89 km from Downtown Winter Garden
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 3 bars/lounges. Our guests praise the pool and the restaurant in ...
Caribe Royale Orlando

Caribe Royale Orlando

4.5 out of 5
8101 World Center Dr, Orlando, FL
24.91 km from Downtown Winter Garden
Book a stay at this luxury hotel in Orlando. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the restaurant in our ...
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL
27.89 km from Downtown Winter Garden
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Jul 9 - Sun, Jul 13
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$110 Roundtrip, found 6 days ago
$110
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Jul 9 from Philadelphia Intl. to Orlando Intl., returning Sun, Jul 13, priced at $110 found 6 days ago
Spirit Airlines
Thu, Sep 18 - Thu, Sep 25
ORD
O'Hare Intl.
MCO
Orlando Intl.
$120 Roundtrip, found 6 days ago
$120
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 25, priced at $120 found 6 days ago
Spirit Airlines
Sat, Jul 5 - Thu, Jul 10
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$120 Roundtrip, found 12 hours ago
$120
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Sat, Jul 5 from Newark Liberty Intl. Airport to Orlando Intl., returning Thu, Jul 10, priced at $120 found 12 hours ago
Frontier Airlines
Sat, Jul 12 - Sat, Jul 19
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Detroit Metropolitan Wayne County to Orlando Intl., returning Sat, Jul 19, priced at $128 found 3 days ago